Essential questions mentors need to ask

You’re stepping up to mentor someone – well done.
Having worked with employers and professional groups over several years to support their schemes, I’ve learned that the likelihood of a successful mentoring relationship is set at the start. If it gets off on the wrong foot, it can be hard to sustain. But if the very first conversation is honest and thorough it can be transformational.

Q. What do you need to cover in that initial conversation with your mentee*?

A. Quite a lot that’s vital for both of you.

If you’re not careful, that first conversation can stay stuck at the social basics: where you’re from, how long you’ve done the job, they’ve done the job, who you both know… Good-to-know stuff for sure, but remember why you’re both there (you might like to refresh your memory by reading ‘So you want to be a mentor?’).

Here are four questions you need to ask your mentee right at the start:

“What’s your understanding of ‘mentoring’?”

Whilst there may have been a formal briefing for mentors and mentees, covering definitions and process, it’s important to check the mentee’s understanding. For example, if they’re seeking counselling they need to take another route (probably via HR). Starting with the mentee’s perception can help you both get clear on what mentoring is – and isn’t. Yes, it’s supporting someone’s development and progress. No, it’s not lobbying management for the mentee’s promotion, etc. Clarify what you can and will do – and what you can’t or won’t.

“What do you want to achieve?”

Much of the initial discussion between mentor and mentee is about goals. The mentee may have prepared a short list of clear goals (always a good start) or may have several vague ideas. This is where the mentor can use coaching questions to help the mentee craft goals that are clear and motivating.

“On a scale of 1-10, how committed are you to this?”

If your mentee’s response is, “er…um… probably 5 or maybe 6…” we have a problem. They may be wary about the process and unsure about what’s expected of them – if so, it’s back to Q1. They may be concerned about time and workload, or lack confidence, skills or knowledge. You’ll need to ask further questions to draw this out and challenge their commitment levels. “What would need to be true for you for that number to be higher?” or “What’s stopping you saying a higher number?” Remember, you’re committed to being a mentor, so you’re perfectly entitled to test out your mentee’s commitment level. Your mentee may find this post useful: ‘Should you get a mentor?’

“What are you willing to do in the next 7 days?”

This question tests the mentee’s commitment to take action following your conversation. There can be a gap between what they say in your discussions and what they actually do. Asking this question adds impetus and supports the mentee to figure out what small steps they can take to get started in the week ahead.

Got a question about mentoring? Please get in touch about how I can help with setting up your scheme and training mentors.

*Yes, it’ a clunky word, but at least it’s clear.


Dawn is the author of ‘The Feedback Book’ and ‘How to be Zoomly at work’

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Image credit: Question mark made from smaller question marks – Orson-DepositPhotos

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